反应详情

2',3'-Dihydroxy-acetophenone (7.5 g, 49 mmole) is dissolved in 303 ml dry tetrahydrofuran in a flame dried 1,000 ml three neck round bottom flask under nitrogen. The solution is treated rapidly dropwise with potassium t-butoxide (1.0 M/THF) (197 ml, 197 mmole) and is mechanically stirred vigorously as methyl-2-(4-morpholinyl)-acetate (10.2 g, 64 mmole) is added neat. The reaction mixture is heated at reflux for 48 h, is treated with a second lot of methyl-2-(4-morpholinyl)-acetate (7 g, 44 mmole), and is stirred an additional 24h at reflux. The reaction is cooled to room temperature, is diluted with 200 ml water, and the tetrahydrofuran is removed in vacuo. The pH of the aqueous residue is adjusted to 6.8 with 10% hydrochloric acid and the mixture is extracted with 5×100 ml dichloromethane. The combined organics are dried over magnesium sulfate and are concentrated in vacuo to a brown solid. The solid is washed with 200 ml diethyl ether and is dried to afford 8.8 g of a tan solid. The solid is recrystallized twice from ethyl acetate to provide 7.5 g (60%) of the title compound as an off-white solid, mp. 202.5° C.

1. dry with materialdried 1,000 ml three neck round bottom flask under nitrogen
2. additionis added neat
3. temperatureThe reaction mixture is heated
4. temperatureat reflux for 48 h
5. temperatureat reflux
6. customthe tetrahydrofuran is removed in vacuo
7. extractionthe mixture is extracted with 5×100 ml dichloromethane
8. dry with materialThe combined organics are dried over magnesium sulfate
9. concentrationare concentrated in vacuo to a brown solid
10. washThe solid is washed with 200 ml diethyl ether
11. customis dried